Selective herbicides based on substituted thien-3-yl-sulphonylamino(thio)carbonyltriazolin(thi)ones and safeners

ABSTRACT

The invention relates to selective herbicidal compositions that comprise an effective amount of an active compound combination comprising
     (a) one or more compounds of the formula (I)   

     
       
         
         
             
             
         
       
         
         in which Q 1 , Q 2 , R 1 , R 2 , R 3  and R 4  are as defined in the disclosure—and salts of the compounds of the formula (I)— 
         and 
         (b) at least one of the crop-plant-compatibility-improving compounds listed in the disclosure. 
       
    
     The invention further relates to the use of these compositions for controlling undesirable vegetation and to a process for preparing the compositions according to the invention.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a Continuation of U.S. application Ser. No.10/489,092, filed Sep. 7, 2004, which is a §371 National StageApplication of PCT/EP2002/010104, filed Sep. 10, 2002, which claimspriority to German Application No. 101 46 590.4, filed Sep. 21, 2001,the content of all of which are incorporated herein by reference intheir entireties.

BACKGROUND

1. Field of the Invention

The invention relates to novel selective herbicidal active compoundcombinations which comprise substitutedthien-3-ylsulphonylamino(thio)carbonyltriazolin(ethi)ones and at leastone compound which improves crop plant compatibility and which can beused with particularly good results for the selective control of weedsin various crops of useful plants.

2. Description of Related Art

Substituted thien-3-ylsulphonylamino(thio)carbonyltriazoline(ethi)onesare already known as effective herbicides (cf. WO-A-01/05788). However,the activity of these compounds and/or their compatibility with cropplants are not entirely satisfactory under all conditions.

SUMMARY

Surprisingly, it has now been found that certain substitutedthien-3-ylsulphonylamino(thio)carbonyltriazolin(ethi)ones, when usedtogether with the crop-plant-compatibility-improving compounds(safeners/antidotes) described below, prevent damage to crop plantsextremely well and can be used particularly advantageously asbroad-spectrum combination preparations for the selective control ofweeds in crops of useful plants, such as, for example, in cereals andmaize.

The invention provides selective herbicidal compositions, characterizedby an effective amount of an active compound combination comprising

-   (a) substituted    thien-3-ylsulphonylamino(thio)carbonyltriazolin(ethi)ones of the    formula (I)

-   in which-   Q¹ represents O (oxygen) or S (sulphur),-   Q² represents O (oxygen) or S (sulphur),-   R¹ represents optionally cyano-, halogen- or    C₁-C₄-alkoxy-substituted alkyl having 1 to 6 carbon atoms,    represents in each case optionally cyano- or halogen-substituted    alkenyl or alkynyl having in each case 2 to 6 carbon atoms,    represents in each case optionally cyano-, halogen- or    C₁-C₄-alkyl-sub-stituted cycloalkyl or cycloalkylalkyl having in    each case 3 to 6 carbon atoms in the cycloalkyl group and, if    appropriate, 1 to 4 carbon atoms in the alkyl moiety, represents in    each case optionally nitro-, cyano-, halogen-, C₁-C₄-alkyl- or    C₁-C₄-alkoxy-substituted aryl or arylalkyl having in each case 6 or    10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon    atoms in the alkyl moiety, or represents in each case optionally    nitro-, cyano-, halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted    heterocyclyl or heterocyclylalkyl having in each case up to 6 carbon    atoms and additionally 1 to 4 nitrogen atoms and/or 1 or 2 oxygen or    sulphur atoms in the heterocyclyl group and, if appropriate, 1 to 4    carbon atoms in the alkyl moiety,-   R² represents hydrogen, cyano, nitro, halogen, represents in each    case optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl,    alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl    having in each case 1 to 6 carbon atoms in the alkyl group, or    represents in each case optionally cyano- or halogen-substituted    alkenyl, alkynyl, alkenyloxy or alkynyloxy having in each case 2 to    6 carbon atoms in the alkenyl or alkynyl group,-   R³ represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine,    chlorine, bromine, iodine, represents optionally fluorine-,    chlorine-, bromine-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- or    C₁-C₄-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms,    represents in each case optionally fluorine-, chlorine- and/or    bromine-substituted alkenyl or alkynyl having in each case 2 to 6    carbon atoms, represents in each case optionally fluorine-,    chlorine-, cyano-, C₁-C₄-alkoxy- or    C₁-C₄-alkoxy-carbonyl-substituted alkoxy, alkylthio, alkylamino or    alkylcarbonylamino having in each case 1 to 6 carbon atoms in the    alkyl group, represents alkenyloxy, alkynyloxy, alkenylthio,    alkynylthio, alkenylamino or alkynylamino having in each case 3 to 6    carbon atoms in the alkenyl or alkynyl group, represents    dialkylamino having in each case 1 to 4 carbon atoms in the alkyl    groups, represents in each case optionally methyl- and/or    ethyl-substituted aziridino, pyrrolidino, piperidino and/or    morpholino, represents in each case optionally fluorine-, chlorine-,    bromine-, cyano- and/or C₁-C₄-alkyl-substituted cycloalkyl,    cycloalkenyl, cycloalkyloxy, cyclo-alkylthio, cycloalkylamino,    cycloalkylalkyl, cycloalkylalkoxy, cycloalkyl-alkylthio or    cycloalkylalkylamino having in each case 3 to 6 carbon atoms in the    cycloalkyl or cycloalkenyl group and, if appropriate, 1 to 4 carbon    atoms in the alkyl moiety, or represents in each case optionally    fluorine-, chlorine-, bromine-, cyano-, nitro-, C₁-C₄-alkyl-,    trifluoromethyl-, C₁-C₄-alkoxy- and/or    C₁-C₄-alkoxy-carbonyl-substituted aryl, arylalkyl, aryloxy,    arylalkoxy, aryl-thio, arylalkylthio, arylamino or arylalkylamino    having in each case 6 or 10 carbon atoms in the aryl group and, if    appropriate, 1 to 4 carbon atoms in the alkyl moiety,-   R⁴ represents hydrogen, hydroxyl, amino, cyano, represents    C₂-C₁₀-alkylidene-amino, represents optionally fluorine-, chlorine-,    bromine-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- or    C₁-C₄-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms,    represents in each case optionally fluorine-, chlorine- and/or    bromine-substituted alkenyl or alkynyl having in each case 2 to 6    carbon atoms, represents in each case optionally fluorine-,    chlorine-, bromine-, cyano-, C₁-C₄-alkoxy- or    C₁-C₄-alkoxy-carbonyl-substituted alkoxy, alkylamino or    alkyl-carbonylamino having in each case 1 to 6 carbon atoms in the    alkyl group, represents alkenyloxy having 3 to 6 carbon atoms,    represents dialkylamino having in each case 1 to 4 carbon atoms in    the alkyl groups, represents in each case optionally fluorine-,    chlorine-, bromine-, cyano- and/or C₁-C₄-alkyl-substituted    cycloalkyl, cycloalkylamino or cyclo-alkylalkyl having in each case    3 to 6 carbon atoms in the alkyl group and, if appropriate, 1 to 4    carbon atoms in the alkyl moiety, or represents in each case    optionally fluorine-, chlorine-, bromine-, cyano- nitro-,    C₁-C₄-alkyl-, trifluoromethyl- and/or C₁-C₄-alkoxy-substituted aryl    or arylalkyl having in each case 6 or 10 carbon atoms in the aryl    group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety,    or-   R³ and R⁴ together represent optionally branched alkanediyl having 3    to 6 carbon atoms,-   —and salts of the compounds of the formula (I)—-   (“active compounds of group 1”)-   and-   (b) at least one compound which improves crop plant compatibility,    from the group of compounds below:    -   4-dichloroacetyl-1-oxa-4-aza-spiro[4.5]-decane (AD-67,        MON-4660),        1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrolo[1,2-a]-pyrimidin-6(2H)-one        (dicyclonon, BAS-145138),        4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine        (benoxacor), 1-methyl-hexyl 5-chloro-quinolin-8-oxy-acetate        (cloquintocet-mexyl—cf. also related compounds in EP-A-86750,        EP-A-94349, EP-A-191736, EP-A-492366),        3-(2-chloro-benzyl)-1-(1-methyl-1-phenyl-ethyl)-urea        (cumyluron), α-(cyanomethoximino)-phenylacetonitrile        (cyometrinil), 2,4-dichloro-phenoxyacetic acid (2,4-D),        4-(2,4-dichloro-phenoxy)-butyric acid (2,4-DB),        1-(1-methyl-1-phenyl-ethyl)-3-(4-methyl-phenyl)-urea (daimuron,        dymron), 3,6-dichloro-2-methoxy-benzoic acid (dicamiba),        S-1-methyl-1-phenyl-ethyl piperidine-1-thiocarboxylate        (dimepiperate),        2,2-dichloro-N-(2-oxo-2-(2-propenylamino)-ethyl)-N-(2-propenyl)-acetamide        (DKA-24), 2,2-dichloro-N,N-di-2-propenyl-acetamide (dichlormid),        4,6-dichloro-2-phenyl-pyrimidine (fenclorim), ethyl        1-(2,4-dichloro-phenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate        (fenchlorazole-ethyl—cf. also related compounds in EP-A-174562        and EP-A-346620), phenyl-methyl        2-chloro-4-trifluoromethyl-thiazole-5-carboxylate (flurazole);        4-chloro-N-(1,3-dioxolan-2-yl-methoxy)-α-trifluoro-acetophenone        oximne (fluxofenim),        3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidine        (furilazole, MON-13900), ethyl        4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate        (isoxadifen-ethyl—cf. also related compounds in WO-A-95/07897),        1-(ethoxycarbonyl)-ethyl-3,6-dichloro-2-methoxybenzoate        (lactidichlor), (4-chloro-o-tolyloxy)-acetic acid (MCPA),        2-(4-chloro-o-tolyloxy)-propionic acid (mecoprop), diethyl        1-(2,4-dichloro-phenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate        (mefenpyr-diethyl—cf. also related compounds in WO-A-91/07874),        2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),        2-propenyl-1-oxa-4-azaspiro[4.5]decane 4-carbodithioate        (MG-838), 1,8-naphthalic anhydride,        α-(1,3-dioxolan-2-yl-methoximino)-phenylacetonitrile        (oxabetinil),        2,2-dichloro-N-(1,3-dioxolan-2-yl-methyl)-N-(2-propenyl)-acetamide        (PPG-1292), 3-dichloroacetyl-2,2-dimethyl-oxazolidine (R-28725),        3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148),        4-(4-chloro-o-tolyl)-butyric acid, 4-(4-chloro-phenoxy)-butyric        acid, diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate        (MON-7400, cf. U.S. Pat. No. 4,964,893), ethyl        diphenylmethoxyacetate, methyl        1-(2-chloro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl        1-(2,4-dichloro-phenyl)-5-methyl-1H-pyrazole-3-carboxylate,        ethyl        1-(2,4-dichloro-phenyl)-5-isopropyl-11H-pyrazole-3-carboxylate,        ethyl        1-(2,4-dichloro-phenyl)-5-(1,1-dimethyl-ethyl)-1H-pyrazole-3-carboxylate,        ethyl 1-(2,4-dichloro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylate        (cf. also related compounds in EP-A-269806 and EP-A-333131),        ethyl 5-(2,4-dichloro-benzyl)-2-isoxazoline-3-carboxylate, ethyl        5-phenyl-2-isoxazoline-3-carboxylate, ethyl        5-(4-fluoro-phenyl)-5-phenyl-2-isoxazoline-3-carboxylate (cf.        also related compounds in WO-A-91/08202), 1,3-dimethyl-but-1-yl        5-chloro-quinolin-8-oxy-acetate, 4-allyloxy-butyl        5-chloro-quinolin-8-oxy-acetate, 1-allyloxy-prop-2-yl        5-chloro-quinolin-8-oxy-acetate, methyl        5-chloro-quinolin-8-oxy-acetate, ethyl        5-chloro-quinolin-8-oxy-acetate, allyl        5-chloro-quinolin-8-oxy-acetate, 2-oxo-prop-1-yl        5-chloro-quinolin-8-oxy-acetate, diethyl        5-chloro-quinolin-8-oxy-malonate, diallyl        5-chloro-quinolin-8-oxy-malonate, diethyl        5-chloro-quinolin-8-oxy-malonate (cf. also related compounds in        EP-A-582 198), 4-carboxy-chroman-4-yl-acetic acid (AC-304415,        cf. EP-A-613618), 4-chloro-phenoxyacetic acid,        3,3′-dimethyl-4-methoxy-benzophenone,        1-bromo-4-chloromethylsulphonyl-benzene,        1-[4-(N-2-methoxybenzoylsulphamoyl)-phenyl]-3-methyl-urea (alias        N-(2-methoxy-benzoyl)-4-[(methylamino-carbonyl)-amino]-benzenesulphonamide),        1-[4-(N-2-methoxybenzoylsulphamoyl)-phenyl]-3,3-dimethyl-urea,        1-[4-(N-4,5-dimethylbenzoylsulphamioy)-phenyl]-3-methyl-urea,        1-[4-(N-naphthylsulphamoyl)-phenyl]-3,3-dimethyl-urea,        N-(2-methoxy-5-methyl-benzoyl)-4-(cyclopropyl-aminocarbonyl)-benzenesulphonamide,-   and/or the following compounds-   of the formula (IIa)

-   or the formula (IIb)

-   or the formula (IIc)

-   where-   n represents a number between 0 and 5,-   A¹ represents one of the divalent heterocyclic groupings shown    below,

-   A² represents optionally C₁-C₄-alkyl- and/or    C₁-C₄-alkoxy-carbonyl-substituted alkanediyl having 1 or 2 carbon    atoms,-   R⁵ represents hydroxyl, mercapto, amino, C₁-C₆-alkoxy,    C₁-C₆-alkylthio, C₁-C₆-alkylamino or di-(C₁-C₄-alkyl)-amino,-   R⁶ represents hydroxyl, mercapto, amino, in each case optionally    C₁-C₄-alkyl, C₁-C₄-alkoxy or C₂-C₄-alkenoxy-substituted    C₁-C₆-alkoxy, C₂-C₆-alkenoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino or    di-(C₁-C₄-alkyl)-amino,-   R⁷ represents in each case optionally fluorine-, chlorine- and/or    bromine-substituted C₁-C₄-alkyl,-   R⁸ represents hydrogen, in each case optionally fluorine-, chlorine-    and/or bromine-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl or    C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, dioxolanyl-C₁-C₄-alkyl,    furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl, piperidinyl, or    optionally fluorine-, chlorine- and/or bromine- or    C₁-C₄-alkyl-substituted phenyl,-   R⁹ represents hydrogen, in each case optionally fluorine-, chlorine-    and/or bromine-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl or    C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, dioxolanyl-C₁-C₄-alkyl,    furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl, piperidinyl, or    optionally fluorine-, chlorine- and/or bromine- or    C₁-C₄-alkyl-substituted phenyl, or together with R⁸ represents    C₃-C₆-alkanediyl or C₂-C₅-oxaalkanediyl, each of which is optionally    substituted by C₁-C₄-alkyl, phenyl, furyl, a fused-on benzene ring    or by two substituents which together with the C atom to which they    are attached form a 5- or 6-membered carbocycle,-   R¹⁰ represents hydrogen, cyano, halogen, or represents in each case    optionally fluorine, chlorine- and/or bromine-substituted    C₁-C₄-alkyl, C₃-C₆-cycloalkyl or phenyl,-   R¹¹ represents hydrogen, optionally hydroxyl-, cyano-, halogen- or    C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, C₃-C₆-cycloalkyl or    tri-(C₁-C₄-alkyl)-silyl,-   R¹² represents hydrogen, cyano, halogen, or represents in each case    optionally fluorine-, chlorine- and/or bromine-substituted    C₁-C₄-alkyl, C₃-C₆-cycloalkyl or phenyl,-   X¹ represents nitro, cyano, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,    C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,-   X² represents hydrogen, cyano, nitro, halogen, C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,-   X³ represents hydrogen, cyano, nitro, halogen, C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,-   where X¹ is preferably found at the (2) and (4) positions, X² is    preferably found at the (5) position and X³ is found at the (2)    position, and/or the following compounds-   of the formula (IId)

-   or the formula (IIe)

-   where-   n again represents a number between 0 and 5,-   R¹³ represents hydrogen or C₁-C₄-alkyl,-   R¹⁴ represents hydrogen or C₁-C₄-alkyl,-   R¹⁵ represents hydrogen, in each case optionally cyano-, halogen- or    C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,    C₁-C₆-alkylamino or di-(C₁-C₄-alkyl)-amino, or in each case    optionally cyano-, halogen- or C₁-C₄-alkyl-substituted    C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio or    C₃-C₆-cycloalkylamino,-   R¹⁶ represents hydrogen, optionally cyano-, hydroxyl-, halogen- or    C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in each case optionally cyano-    or halogen-substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl, or optionally    cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl,-   R¹⁷ represents hydrogen, optionally cyano-, hydroxyl-, halogen- or    C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in each case optionally cyano-    or halogen-substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl, optionally    cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, or    optionally nitro-, cyano, halogen-, C₁-C₄-alkyl-,    C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- or    C₁-C₄-halogenoalkoxy-substituted phenyl, or together with R¹⁶    represents in each case optionally C₁-C₄-alkyl-substituted    C₂-C₆-alkanediyl or C₂-C₅-oxaalkanediyl,-   X⁴ represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl.    hydroxyl, amino, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy    or C₁-C₄-haloalkoxy. and-   X⁵ represents nitro, cyano, carboxyl. carbamoyl. formyl, sulphamoyl,    hydroxyl, amino, halogen, C₁-C₄-alkyl, C₁-C₄-haioalkyl, C₁-C₄-alkoxy    or C₁-C₄-haloalkoxy,-   where X⁴ is preferably located in position (2) and/or (5)-   (“active compounds of group 2”).

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

In the definitions, the hydrocarbon chains, such as in alkyl oralkanediyl, are in each case straight-chain or branched—including incombination with hetero atoms, such as in alkoxy.

Preferred meanings of the groups listed above in connection with theformula (I) are defined below.

-   Q¹ preferably represents O (oxygen) or S (sulphur).-   Q² preferably represents O (oxygen) or S (sulphur).-   R¹ preferably represents in each case optionally cyano-, fluorine-,    chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or    i-propyl, n-, i-, s- or tbutyl, represents in each case optionally    cyano-, fluorine- or chlorine-substituted propenyl, butenyl,    propynyl or butynyl, represents in each case optionally cyano-.    fluorine-, chlorine-, methyl- or ethyl-substituted cyclopropyl,    cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,    cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, represents    in each case optionally cyano-, fluorine-, chlorine-, bromine-,    methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-, methoxy-,    ethoxy-, n- or i-propoxy-, difluoromethoxy- or    trifluoromethoxy-substituted phenyl, phenylmethyl or phenyl-ethyl,    or represents in each case optionally cyano-, fluorine-, chlorine-,    bromine-, methyl-, ethyl-, n- or i-propyl-, methoxy-, ethoxy-, n- or    i-propoxy-substituted heterocyclyl or heterocyclylmethyl, where the    heterocyclyl group is in each case selected from the group    consisting of oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl,    tetrahydrothienyl.-   R² represents hydrogen, cyano, fluorine, chlorine, bromine,    represents in each case optionally cyano-, fluorine-, chlorine-,    methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-,    i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,    methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,    methyl-thio, ethylthio, n- or i-propylthio, methylsulphinyl,    ethylsulphinyl, methyl-sulphonyl or ethylsulphonyl, or represents in    each case optionally cyano-, fluorine- or chlorine-substituted    propenyl, butenyl, propynyl, butynyl, propenyloxy, butenyloxy,    propynyloxy or butynyloxy.

R³ represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine,chlorine, bromine, represents in each case optionally fluorine-,chlorine-, cyano-, methoxy-, ethoxy-, n- or i-propoxy-, acetyl-,propionyl-, n- or i-butyroyl. methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxycarbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, represents in each case optionally fluorine-, chlorine-and/or bromine-substituted ethenyl, propenyl, butenyl, ethynyl, propynylor butynyl, represents in each case optionally fluorine-, chlorine-,cyano-, methoxy-, ethoxy-, n- or i-propoxy-, methoxycarbonyl-,ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methoxy, ethoxy, n-or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- ori-propylamino, n-, i-, s- or t-butylamino, acetylamino orpropionylamino, represents propenyloxy, butenyloxy, ethynyloxy,propynyloxy, butynyloxy, propenyl-thio, butenylthio, propynyhhio,butynylthio, propenylamino, butenylamino, propynylamino or butynylamino,represents dimethylamino, diethylamino or dipropylamino, represents ineach case optionally fluorine-, chlorine-, methyl- and/orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy,cyclopentyl-oxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio,cyclopentylthio, cyclo-hexylthio, cyclopropylamino, cyclobutylamino,cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl, cyclo-hexylmethyl, cyclopropylmethoxy,cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy,cyclopropylmethylthio, cyclobutylmethylthio, cyclo-pentylmethylthio,cyclohexylmethylthio, cyclopropylmethylamino, cyclo-butylmethylamino,cyclopentylmethylamino or cyclohexylmethylamino, or represents in eachcase optionally fluorine-, chlorine-, bromine-, methyl-,trifluoromethyl-, methoxy- or methoxycarbonyl-substituted phenyl,benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino orbenzylamino.

-   R⁴ preferably represents hydrogen, hydroxyl, amino, represents in    each case optionally fluorine-, chlorine-, cyano-, methoxy- or    ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or    t-butyl, represents in each case optionally fluorine, chlorine,    and/or bromine-substituted ethenyl, propenyl, butenyl, propynyl or    butynyl, represents in each case optionally fluorine-, chlorine-,    cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or    i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or    i-propylamino, n-, i-, s- or t-butylamino, represents propenyloxy or    butenyloxy, represents di-methylamino or diethylamino, represents in    each case optionally fluorine-, chlorine-, methyl- and/or    ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,    cyclopropylamino, cyclobutylamino, cyclopentylamino,    cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl,    cyclopentylmethyl or cyclohexylmethyl, or represents in each case    optionally fluorine-, chlorine-, methyl-, trifluoromethyl- and/or    methoxy-substituted phenyl or benzyl.-   R³ and R⁴ together preferably represent trimethylene    (propane-1,3-diyl), tetra-methylene (butane-1,4-diyl) or    pentamethylene (pentane-1,5-diyl).-   Q¹ particularly preferably represents O (oxygen).-   Q² particularly preferably represents O (oxygen).-   R¹ particularly preferably represents in each case optionally    fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl,    n- or i-propyl.-   R² particularly preferably represents fluorine, chlorine, bromine or    represents in each case optionally fluorine-, chlorine-, methoxy- or    ethoxy-substituted methyl, ethyl, n- or i-propyl.-   R³ particularly preferably represents hydrogen, chlorine, bromine,    represents in each case optionally fluorine-, chlorine-, methoxy-,    ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl,    represents in each case optionally fluorine- or chlorine-substituted    ethenyl, propenyl, butenyl, propynyl or butynyl, represents in each    case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or    i-propoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio,    ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or    i-propylamino, represents propenyloxy, propynyloxy, propenylthio,    propynyl-thio, propenylamino or propynylamino, represents    dimethylamino or diethylamino, represents in each case optionally    fluorine-, chlorine- or methyl-substituted cyclopropyl,    cyclopropyloxy, cyclopropylmethyl or cyclopropyl-methoxy.-   R⁴ particularly preferably represents in each case optionally    fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl,    n- or i-propyl, represents in each case optionally fluorine- or    chlorine-substituted ethenyl, propenyl or propynyl, represents in    each case optionally fluorine-, chlorine-, methoxy- or    ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, represents    methylamino, or represents cyclopropyl.

Most preferably, R¹ and R² represent methyl, ethyl, n- or i-propyl.

Preferred active compound components of group 1 are in particular alsothe sodium, potassium, magnesium, calcium, ammonium,C₁-C₄-alkylammonium-, di-(C₁-C₄-alkyl)ammonium-,tri-(C₁-C₄-alkyl)ammonium, tetra-(C₁-C₄-alkyl)ammonium,tri-(C₁-C₄-alkyl)sulphonium-, C₅- or C₆-cycloalkylammonium anddi-(C₁-C₂-alkyl)-benzylammonium salts of compounds of the formula (I) inwhich Q¹, Q², R¹, R², R³ and R⁴ have the meanings given above as beingpreferred.

Examples of compounds of the formula (I) which are very particularlypreferred as active compound components according to the invention arelisted in Table I below.

TABLE 1 Examples of compounds of the formula (I) Ex. Melting No. Q¹ Q²R¹ R² R³ R⁴ point (° C.) I-1  O O CH₃ CH₃ OC₂H₅ CH₃ 163 I-2  O O CH₃ CH₃OCH₃ CH₃ 201 I-3  O O CH₃ CH₃ OC₃H₇-n CH₃ 156 I-4  O O CH₃ CH₃ OC₃H₇-iCH₃ 150 I-5  O O CH₃ CH₃ OCH₃

218 I-6  O O CH₃ CH₃ OC₂H₅

170 I-7  O O CH₃ CH₃ OC₃H₇-n

156 I-8  O O CH₃ CH₃ OC₃H₇-i

188 I-9  O O CH₃ CH₃

200 I-10 O O CH₃ CH₃ CH₃ CH₃ 178 I-11 O O CH₃ CH₃ C₂H₅ CH₃ 161 I-12 O OCH₃ CH₃ SCH₃ CH₃ 183 I-13 O O C₂H₅ CH₃ OCH₃ CH₃ 176 I-14 O O CH₃ CH₃CH₂OCH₃

185 I-15 O O C₂H₅ CH₃ OC₂H₅ CH₃ 172 I-16 O O C₂H₅ CH₃ OCH₃

173 I-17 O O CH₃ CH₃ C₂H₅ OC₂H₅ 183 I-18 O O CH₃ CH₃ C₂H₅

175

Very particular emphasis as active compound components according to theinvention is also given to the sodium salts of the compounds from Table1.

Preferred meanings of the groups listed above in connection with thecompounds improving crop plant compatibility (“herbicide safeners”) ofthe formulae (IIa), (IIb), (IIc), (IId) and (IIe) are defined below.

-   n preferably represents the numbers 0, 1, 2, 3 or 4.-   A² preferably represents in each case optionally methyl-, ethyl-,    methoxycarbonyl- or ethoxycarbonyl-substituted methylene or    ethylene.-   R⁵ preferably represents hydroxyl, mercapto, amino, methoxy, ethoxy,    n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n-    or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino,    n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or    diethylamino.-   R⁶ preferably represents hydroxyl, mercapto, amino, methoxy, ethoxy,    n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n-    or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino,    n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or    diethylamino.-   R⁷ preferably represents in each case optionally fluorine-,    chlorine- and/or bromine-substituted methyl, ethyl, n- or i-propyl.-   R⁸ preferably represents hydrogen, in each case optionally fluorine-    and/or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-,    s- or t-butyl, propenyl, butenyl, propynyl or butynyl,    methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl,    dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl,    piperidinyl, or optionally fluorine-, chlorine-, methyl-, ethyl-, n-    or i-propyl-, n-, i-, s- or t-butyl-substituted phenyl.-   R⁹ preferably represents hydrogen, in each case optionally fluorine-    and/or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-,    s- or t-butyl, propenyl, butenyl, propynyl or butynyl,    methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl,    dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl,    piperidinyl, or optionally fluorine-, chlorine-, methyl-, ethyl-, n-    or i-propyl-, n-, i-, s- or t-butyl-substituted phenyl, or together    with R⁸ represents one of the radicals —CH₂—O—CH₂—CH₂— and    —CH₂—CH₂—O—CH₂—CH₂−, which are optionally substituted by methyl,    ethyl, furyl, phenyl, a fused-on benzene ring or by two substituents    which together with the C atom to which they are attached form a 5-    or 6-membered carbocycle.-   R¹⁰ preferably represents hydrogen, cyano, fluorine, chlorine,    bromine, or represents in each case optionally fluorine-, chlorine-    and/or bromine-substituted methyl, ethyl, n- or i-propyl,    cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl.-   R¹¹ preferably represents hydrogen, optionally hydroxyl-, cyano-,    fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted    methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.-   R¹² preferably represents hydrogen, cyano, fluorine, chlorine,    bromine, or represents in each case optionally fluorine-, chlorine-    and/or bromine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-    or t-butyl, cyclopropyl, cyclobuty), cyclopentyl, cyclohexyl or    phenyl.-   X¹ preferably represents nitro, cyano, fluorine, chlorine, bromine,    methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,    difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl,    chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or    i-propoxy, difluoromethoxy or trifluoromethoxy.-   X² preferably represents hydrogen, nitro, cyano, fluorine, chlorine,    bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,    difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl,    chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or    i-propoxy, difluoromethoxy or trifluoromethoxy.-   X³ preferably represents hydrogen, nitro, cyano, fluorine, chlorine,    bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,    difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl,    chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or    i-propoxy, difluoromethoxy or trifluoromethoxy.-   R¹³ preferably represents hydrogen, methyl, ethyl, n- or i-propyl.-   R¹⁴ preferably represents hydrogen, methyl, ethyl, n- or i-propyl.-   R¹⁵ preferably represents hydrogen, in each case optionally cyano-,    fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted    methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy,    ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio,    ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,    methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or    t-butylamino, dimethylamino or diethylamino, or in each case    optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-,    n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,    cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy,    cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio,    cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino    or cyclohexylamino.-   R¹⁶ preferably represents hydrogen, in each case optionally cyano-,    hydroxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or    i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or    s-butyl, in each case optionally cyano-, fluorine-, chlorine- or    bromine-substituted propenyl, butenyl, propynyl or butynyl, or in    each case optionally cyano-, fluorine-, chlorine-, bromine-,    methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl,    cyclopentyl or cyclohexyl.-   R¹⁷ preferably represents hydrogen, represents in each case    optionally cyano-, hydroxyl-, fluorine-, chlorine-, methoxy-,    ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl,    n-, i- or s-butyl, in each case optionally cyano-, fluorine-,    chlorine- or bromine-substituted propenyl, butenyl, propynyl or    butynyl, in each case optionally cyano-, fluorine-, chlorine-,    bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl,    cyclobutyl, cyclopentyl or cyclohexyl, or optionally nitro-, cyano-,    fluorine-, chlorine-, bromine-, methyl, ethyl-, n- or i-propyl-, n-,    i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or    i-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl,    or together with R¹⁶ represents in each case optionally methyl- or    ethyl-substituted butane-1,4-diyl (trimethylene), pentane-1,5-diyl,    1-oxa-butane-1,4-diyl or 3-oxa-pentane-1,5-diyl.-   X⁴ preferably represents nitro, cyano, carboxyl, carbamoyl, formyl,    sulphamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl,    ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl,    methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or    trifluoromethoxy.-   X⁵ preferably represents nitro, cyano, carboxyl, carbamoyl, formyl,    sulphamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl,    ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl,    methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or    trifluoromethoxy.

Examples of compounds of the formula (IIa) which are very particularlypreferred as herbicide safeners according to the invention are listed inTable 2 below.

TABLE 2 Examples of the compounds of the formula (IIa) (IIa)

Example (positions) No. (X¹)_(n) A¹ R⁵ IIa-1  (2) Cl, (4) Cl

OCH₃ IIa-2  (2) Cl, (4) Cl

OCH₃ IIa-3  (2) Cl, (4) Cl

OC₂H₅ IIa-4  (2) Cl, (4) Cl

OC₂H₅ IIa-5  (2) Cl

OCH₃ IIa-6  (2) Cl, (4) Cl

OCH₃ IIa-7  (2) F

OCH₃ IIa-8  (2) F

OCH₃ IIa-9  (2) Cl, (4) Cl

OC₂H₅ IIa-10 (2) Cl, (4) CF₃

OCH₃ IIa-11 (2) Cl

OCH₃ IIa-12 —

OC₂H₅ IIa-13 (2) Cl, (4) Cl

OC₂H₅ IIa-14 (2) Cl, (4) Cl

OC₂H₅ IIa-15 (2) Cl, (4) Cl

OC₂H₅ IIa-16 (2) Cl, (4) Cl

OC₂H₅ IIa-17 (2) Cl, (4) Cl

OC₂H₅

Examples of compounds of the formula (IIb) which are very particularlypreferred as herbicide safeners according to the invention are listed inTable 3 below.

TABLE 3 Examples of compounds of the formula (IIb) (IIb)

Ex- (posi- (posi- ample tion) tion) No. X² X³ A² R⁶ IIb-1  (5) Cl — CH₂OH IIb-2  (5) Cl — CH₂ OCH₃ IIb-3  (5) Cl — CH₂ OC₂H₅ IIb-4  (5) Cl —CH₂ OC₃H₇-n IIb-5  (5) Cl — CH₂ OC₃H₇-i IIb-6  (5) Cl — CH₂ OC₄H₉-nIIb-7  (5) Cl — CH₂ OCH(CH₃)C₅H₁₁-n IIb-8  (5) Cl (2) F CH₂ OH IIb-9 (5) Cl (2) Cl CH₂ OH IIb-10 (5) Cl — CH₂ OCH₂CH═CH₂ IIb-11 (5) Cl — CH₂OC₄H₉-i IIb-12 (5) Cl — CH₂

IIb-13 (5) Cl —

OCH₂CH═CH₂ IIb-14 (5) Cl —

OC₂H₅

Examples of the compounds (IIc) which are very particularly preferred asherbicide safeners according to the invention are listed in Table 4below.

TABLE 4 Examples of the compounds of the formula (IIc) (IIc)

Example No. R⁷ N(R⁸, R⁹) IIc-1 CHCl₂ N(CH₂CH═CH₂)₂ IIc-2 CHCl₂

IIc-3 CHCl₂

IIc-4 CHCl₂

IIc-5 CHCl₂

IIc-6 CHCl₂

IIc-7 CHCl₂

Examples of the compounds of the formula (IId) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in Table 5 below.

TABLE 5 Examples of the compounds of the formula (IId) (IId)

Example (positions) (positions) No. R¹³ R¹⁴ R¹⁵ (X⁴)_(n) (X⁵)_(n) IId-1 H H CH₃ (2) OCH₃ — IId-2  H H C₂H₅ (2) OCH₃ — IId-3  H H C₃H₇-n (2) OCH₃— IId-4  H H C₃H₇-i (2) OCH₃ — IId-5  H H

(2) OCH₃ — IId-6  H H CH₃ (2) OCH₃ (5) CH₃ — IId-7  H H C₂H₅ (2) OCH₃(5) CH₃ — IId-8  H H C₃H₇-n (2) OCH₃ (5) CH₃ — IId-9  H H C₃H₇-i (2)OCH₃ (5) CH₃ — IId-10 H H

(2) OCH₃ (5) CH₃ — IId-11 H H OCH₃ (2) OCH₃ (5) CH₃ — IId-12 H H OC₂H₅(2) OCH₃ (5) CH₃ — IId-13 H H OC₃H₇-i (2) OCH₃ (5) CH₃ — IId-14 H H SCH₃(2) OCH₃ (5) CH₃ — IId-15 H H SC₂H₅ (2) OCH₃ (5) CH₃ — IId-16 H HSC₃H₇-i (2) OCH₃ (5) CH₃ — IId-17 H H NHCH₃ (2) OCH₃ (5) CH₃ — IId-18 HH NHC₂H₅ (2) OCH₃ (5) CH₃ — IId-19 H H NHC₃H₇-i (2) OCH₃ (5) CH₃ —IId-20 H H

(2) OCH₃ (5) CH₃ — IId-21 H H NHCH₃ (2) OCH₃ — IId-22 H H NHC₃H₇-i (2)OCH₃ — IId-23 H H N(CH₃)₂ (2) OCH₃ — IId-24 H H N(CH₃)₂ (3) CH₃ (4) CH₃— IId-25 H H CH₂OCH₃ (2) OCH₃ — IId-26 H H CH₂OCH₃ (2) OCH₃ (5) CH₃ —

Examples of the compounds of the formula (IIe) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in Table 6 below.

TABLE 6 Examples of the compounds of the formula (IIe) (IIe)

Example (positions) (positions) No. R¹³ R¹⁶ R¹⁷ (X⁴)_(n) (X⁵)_(n) IIe-1 H H CH₃ (2) OCH₃ — IIe-2  H H C₂H₅ (2) OCH₃ — IIe-3  H H C₃H₇-n (2) OCH₃— IIe-4  H H C₃H₇-i (2) OCH₃ — IIe-5  H H

(2) OCH₃ — IIe-6  H H CH₃ (2) OCH₃ — IIe-7  H H CH₃ (2) OCH₃ (5) CH₃ —IIe-8  H H C₂H₅ (2) OCH₃ (5) CH₃ — IIe-9  H H C₃H₇-n (2) OCH₃ (5) CH₃ —IIe-10 H H C₃H₇-i (2) OCH₃ (5) CH₃ — IIe-11 H H

(2) OCH₃ (5) CH₃ — IIe-12 H H CH₃ (2) OCH₃ (5) CH₃ — IIe-13 H HCH₂CH═CH₂ (2) OCH₃ — IIe-14 H H CH₂CH═CH₂ (2) OCH₃ (5) CH₃ — IIe-15 H H

(2) OCH₃ — IIe-16 H H

(2) OCH₃ (5) CH₃ — IIe-17 H H

(2) OCH₃ — IIe-18 H H

(2) OCH₃ (5) CH₃ — IIe-19 H H

(2) OCH₃ — IIe-20 H H

(2) OCH₃ (5) CH₃ —

The compounds of the general formula (IIa) to be used as safenersaccording to the invention are known and/or can be prepared by processesknown per se (cf. WO-A-91/07874, WO-A-95/07897).

The compounds of the general formula (IIb) to be used as safenersaccording to the invention are known and/or can be prepared by processesknown per se (cf. EP-A-191736).

The compounds of the general formula (IIc) to be used as safenersaccording to the invention are known and/or can be prepared by processesknown per se (cf. DE-A-22180974, DE-A-2350547).

The compounds of the general formula (IId) to be used as safenersaccording to the invention are known and/or can be prepared by processesknown per se (cf. DE-A-19621522/U.S. Pat. No. 6,235,680/WO 97/4016).

The compounds of the general formula (IIe) to be used as safenersaccording to the invention are known and/or can be prepared by processesknown per se (cf. WO-A-99/66795/U.S. Pat. No. 6,251,827).

Examples of the selectively herbicidal combinations according to theinvention of in each case one active compound of the formula (I) and ineach case one of the safeners defined above are listed in Table 7 below.

TABLE 7 Examples of combinations according to the invention Activecompound of the formula (I) Safener I-1 AD-67 I-1 cloquintocet-mexyl I-1dichlormid I-1 fenchlorazole-ethyl I-1 isoxadifen-ethyl I-1mefenpyr-diethyl I-1 MON-7400 I-1 flurazole I-1 furilazole I-1 fenclorimI-1 cumyluron I-1 daimuron/dymron I-1 dimepiperate I-1 IId-25 I-1 IIe-11I-2 AD-67 I-2 cloquintocet-mexyl I-2 dichlormid I-2 fenchlorazole-ethylI-2 isoxadifen-ethyl I-2 mefenpyr-diethyl I-2 MON-7400 I-2 flurazole I-2furilazole I-2 fenclorim I-2 cumyluron I-2 daimuron/dymron I-2dimepiperate I-2 IId-25 I-2 IIe-11 I-3 AD-67 I-3 cloquintocet-mexyl I-3dichlormid I-3 fenchlorazole-ethyl I-3 isoxadifen-ethyl I-3mefenpyr-diethyl I-3 MON-7400 I-3 flurazole I-3 furilazole I-3 fenclorimI-3 cumyluron I-3 daimuron/dymron I-3 dimepiperate I-3 IId-25 I-3 IIe-11I-4 AD-67 I-4 cloquintocet-mexyl I-4 dichlormid I-4 fenchlorazole-ethylI-4 isoxadifen-ethyl I-4 mefenpyr-diethyl I-4 MON-7400 I-4 flurazole I-4furilazole I-4 fenclorim I-4 cumyluron I-4 daimuron/dymron I-4dimepiperate I-4 IId-25 I-4 IIe-11 I-5 AD-67 I-5 cloquintocet-mexyl I-5dichlormid I-5 fenchlorazole-ethyl I-5 isoxadifen-ethyl I-5mefenpyr-diethyl I-5 MON-7400 I-5 flurazole I-5 furilazole I-5 fenclorimI-5 cumyluron I-5 daimuron/dymron I-5 dimepiperate I-5 IId-25 I-5 IIe-11I-6 AD-67 I-6 cloquintocet-mexyl I-6 dichlormid I-6 fenchlorazole-ethylI-6 isoxadifen-ethyl I-6 mefenpyr-diethyl I-6 MON-7400 I-6 flurazole I-6furilazole I-6 fenclorim I-6 cumyluron I-6 daimuron/dymron I-6dimepiperate I-6 IId-25 I-6 IIe-11 I-7 AD-67 I-7 cloquintocet-mexyl I-7dichlormid I-7 fenchlorazole-ethyl I-7 isoxadifen-ethyl I-7mefenpyr-diethyl I-7 MON-7400 I-7 flurazole I-7 furilazole I-7 fenclorimI-7 cumyluron I-7 daimuron/dymron I-7 dimepiperate I-7 IId-25 I-7 IIe-11I-8 AD-67 I-8 cloquintocet-mexyl I-8 dichlormid I-8 fenchlorazole-ethylI-8 isoxadifen-ethyl I-8 mefenpyr-diethyl I-8 MON-7400 I-8 flurazole I-8furilazole I-8 fenclorim I-8 cumyluron I-8 daimuron/dymron I-8dimepiperate I-8 IId-25 I-8 IIe-11 I-9 AD-67 I-9 cloquintocet-mexyl I-9dichlormid I-9 fenchlorazole-ethyl I-9 isoxadifen-ethyl I-9mefenpyr-diethyl I-9 MON-7400 I-9 flurazole I-9 furilazole I-9 fenclorimI-9 cumyluron I-9 daimuron/dymron I-9 dimepiperate I-9 IId-25 I-9 IIe-11I-10 AD-67 I-10 Cloquintocet-mexyl I-10 dichlormid I-10fenchlorazole-ethyl I-10 isoxadifen-ethyl I-10 mefenpyr-diethyl I-10MON-7400 I-10 flurazole I-10 furilazole I-10 fenclorim I-10 cumyluronI-10 daimuron/dymron I-10 dimepiperate I-10 IId-25 I-10 IIe-11 I-11AD-67 I-11 cloquintocet-mexyl I-11 dichlormid I-11 fenchlorazole-ethylI-11 isoxadifen-ethyl I-11 mefenpyr-diethyl I-11 MON-7400 I-11 flurazoleI-11 furilazole I-11 fenclorim I-11 cumyluron I-11 daimuron/dymron I-11dimepiperate I-11 IId-25 I-11 IIe-11 I-12 AD-67 I-12 cloquintocet-mexylI-12 dichlormid I-12 fenchlorazole-ethyl I-12 isoxadifen-ethyl I-12mefenpyr-diethyl I-12 MON-7400 I-12 flurazole I-12 furilazole I-12fenclorim I-12 cumyluron I-12 daimuron/dymron I-12 dimepiperate I-12IId-25 I-12 IIe-11 I-13 mefenpyr-diethyl I-2, sodium salt IId-25 I-15mefenpyr-diethyl I-16 mefenpyr-diethyl I-17 mefenpyr-diethyl I-14mefenpyr-diethyl I-18 mefenpyr-diethyl

Surprisingly, it has now been found that the above-defined activecompound combinations of substitutedthien-3-ylsulphonylamino(thio)carbonyltriazolin(ethi)ones of the generalformula (I) and/or their salts and safeners (antidotes) of group (2)listed above, whilst being tolerated very well by crop plants, haveparticularly high herbicidal activity and can be used in various crops,in particular in cereal (especially wheat) and maize, but also in soyabeans, potatoes and rice, for the selective control of weeds.

Here, it has to be considered to be surprising that, from a large numberof known safeners or antidotes which are capable of antagonizing thedamaging effect of a herbicide on the crop plants, that are inparticular the abovementioned compounds of group (2) which neutralizethe damaging effect of substitutedthien-3-ylsulphonylamino(thio)carbonyltriazolin(ethi)ones on the cropplants virtually completely without negatively affecting the herbicidalactivity with respect to the weeds.

Emphasis is given here to the particularly advantageous effect of theparticularly and most preferred combination partners from group (2), inparticular in respect of sparing cereal plants, such as, for example,wheat, barley and rye, but also maize and rice, as crop plants.

The active compound combinations according to the invention can be used,for example, in connection with the following plants:

Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium,Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica,Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea,Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum,Rorippa, Rotala, Lindemia, Lamium, Veronica, Abutilon, Emex, Datura,Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cuburbita,Helianthus.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus, Apera.

Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.

However, the use of the active compound combinations according to theinvention is in no way restricted to these genera, but also extends inthe same manner to other plants. According to the invention, crop plantsare all plants and plant varieties including transgenic plants and plantvarieties, where on transgenic plants and plant varieties it is alsopossible for synergistic effects to occur.

The advantageous effect of the crop plant compatibility of the activecompound combinations according to the invention is particularly highlypronounced at certain concentration ratios. However, the weight ratiosof the active compounds in the active compound concentrations can bevaried within relatively wide ranges. In general, 0.001 to 1000 parts byweight, preferably 0.01 to 100 parts by weight, and particularlypreferably 0.1 to 50 parts by weight and most preferably 1 to 25 partsby weight of one of the compounds which improve crop plant compatibilitymentioned under group 2 above (antidotes/safeners) are present per partby weight of active compound of the formula (I) or its salts.

The active compounds or active compound combinations can be convertedinto the customary formulations, such as solutions, emulsions, wettablepowders, suspensions, powders, dusting agents, pastes, soluble powders,granules, suspoemulsion concentrates, natural and synthetic materialsimpregnated with active compound, and very fine capsules in polymericsubstances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants and/or foam-formers.

If the extender used is water, it is also possible to use, for example,organic solvents as auxiliary solvents. Suitable liquid solvents areessentially: aromatics, such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics and chlorinated aliphatic hydrocarbons, such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons, such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols, such as butanol orglycol, and also their ethers and esters, ketones, such as acetone,methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, stronglypolar solvents, such as dimethylformamide and dimethy) sulphoxide, andalso water.

Suitable solid carriers are:

for example ammonium salts and ground natural minerals, such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, ground synthetic minerals, such as finely divided silica, aluminaand silicates, suitable solid carriers for granules are: for examplecrushed and fractionated natural rocks such as calcite, marble, pumice,sepiolite and dolomite, and also synthetic granules of inorganic andorganic meals, and granules of organic material such as sawdust, coconutshells, maize cobs and tobacco stalks; suitable emulsifiers and/orfoam-formers are: for example non-ionic and anionic emulsifiers, such aspolyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers,for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates and protein hydrolysates; suitabledispersants are: for example lignosulphite waste liquors andmethylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, and also naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations generally comprise from 0.1 to 95 percent by weight ofactive compounds including the safeners, preferably between 0.5 and 90%.

The active compound combinations according to the invention aregenerally used in the form of finished formulations. However, the activecompounds contained in the active compound combinations can also bemixed in individual formulations when used, i.e. in the form of tankmixes.

The novel active compound combinations, as such or in theirformulations, can furthermore be used as a mixture with other knownherbicides, finished formulations or tank mixes again being possible. Amixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, growth factors,plant nutrients and agents which improve soil structure, is alsopossible. For certain intended uses, in particular in the post-emergencemethod, it may furthermore be advantageous to include, as furtheradditives in the formulations, mineral or vegetable oils which aretolerated by plants (for example the commercial preparation “RakoBinol”), or ammonium salts such as, for example, ammonium sulphate orammonium thiocyanate.

The novel active compound combinations can be used as such, in the formof their formulations or the use forms prepared therefrom by furtherdilution, such as ready-to-use solutions, suspensions, emulsions,powders, pastes and granules. They are used in the customary manner, forexample by washing, spraying, atomizing, dusting or scattering.

The amounts of the active compound combinations according to theinvention applied can be varied within a certain range; they depend,inter alia. on the weather and on soil factors. In general, theapplication rates are between 0.001 and 5 kg per ha, preferably between0.001 and 1 kg per ha, particularly preferably between 0.003 and 0.5 kgper ha.

The active compound combinations according to the invention can beapplied before and after emergence of the plants, that is to say by thepre-emergence and post-emergence method.

Use Examples

The active compound or safener components are in each case dissolved ina few ml (generally 2-3 ml) of solvent (generally acetone orN,N-dimethyl-formamide), and the solutions are combined and then—ifappropriate after addition of an emulsifier—diluted with water to thedesired concentration. In general, an aqueous spray liquor was preparedusing 0.1% of the additive Renex-36.

Example A Post-Emergence Test

The test plants are grown under controlled conditions (temperature,light, atmospheric humidity) in a greenhouse. The test plants aresprayed when they have reached a height of 5-15 cm. The concentration ofthe spray liquor is chosen such that the particular amounts of activecompound desired are applied in 5001 of water/ha.

After spraying, the pots with the test plants are kept in a greenhousechamber under controlled conditions (temperature, light, atmospherichumidity) until the test has ended. About three weeks after theapplication, the degree of damage to the crop plants is rated in %damage in comparison to the development of the untreated control.

The figures denote:

-   -   0%=no damage (like untreated control)    -   100%=total destruction/damage

Active compounds, application rates, test plants and results are shownin the tables below, the terms being used in the tables being as definedbelow:

maize=maize cv. “Pioneer”a.i.=active ingredient=active compound/safener

TABLE A1 Post-emergence test/greenhouse Active compound Application rateDamage maize (+safener) (g of a.i./ha) (in %) I-2 10 35 I-2 + AD-67 10 +100 7 I-2 + cloquintocet-mexyl 10 + 100 1.5 I-2 + dichlormid 10 + 10013.5 I-2 + fenchlorazole-ethyl 10 + 100 12 I-2 + isoxadifen-ethyl 10 +100 4 I-2 + furilazole 10 + 100 2.5 I-2 + flurazole 10 + 100 4.5 I-2 +IIe-11 10 + 100 2 I-2 + MON-7400 10 + 100 1.5

Example A-2 Post-Emergence Test

Here, an aqueous spray liquor comprising 0.5% of the additive Renex-36was prepared.

TABLE A-2 Post-emergence test/greenhouse Damage winter Application ratebarley (g of a.i./ha) (in %) Active compound (+safener) I-2, sodium salt4 60 2 50 I-2, sodium salt + Comp. No. IId- 4 + 100 50 25 2 + 100 25 4 +30  50 2 + 30  35 Safener Comp. No. IId-25 100 0 30 0

Example A-3 Post-Emergence Test

The compound I-2 was used as 10 WP. In each case, Marlipal® was added inan amount of 500 ml/ha.

Evaluation was carried out as early as 7 days after the application.

Maize 1=maize of the cultivar “Prinz”

Maize 2=maize of the cultivar “Pioneer”

Maize 3=maize of the cultivar “LIXIS”

TABLE A-3 Post-emergence test/greenhouse Application rate Activecompound (+safener) (g of a.i./ha) Damage maize 1 (in %) I-2 15 20 8 10I-2 + Comp. No. IId-25 15 + 100 5  8 + 100 0 Damage maize 2 (in %) I-215 20 8 10 I-2 + Comp. No. IId-25 15 + 100 5  8 + 100 5 Damage Maize 3(in %) I-2 15 40 8 20 I-2 + Comp. No. IId-25 15 + 100 20  8 + 100 1015 + 50  10 8 + 50 10

Example A-4 Post-Emergence Test

Mefenpyr-diethyl was used as 100 EC.

The compounds of Ex. Nos. I-2 and I-13 were used as 10 WP.

TABLE A-4 Post-emergence test/greenhouse Application rate Damage winterSafener (g of a.i./ha) wheat (in %) mefenpyr-diethyl 50 0 Applicationrate Damage winter Active compound (+safener) (g of a.i./ha) wheat (in%) I-2 30 60 15 40 I-2 + mefenpyr-diethyl 30 + 50 10 15 + 50 5 Damagewinter Application rate wheat Active compound (+safener) (g of a.i./ha)(in %) I-13 125  30 60 20 I-13 + mefenpyr-diethyl 125 + 50  10 60 + 50 5Damage winter Application rate wheat Safener (g of a.i./ha) (in %)mefenpyr-diethyl 50 0 Damage winter Application rate barley Activecompound (+safener) (g of a.i./ha) (in %) I-2 30 80 15 70  8 50 I-2 +mefenpyr-diethyl 30 + 50 70 15 + 50 40  8 + 50 30 Damage winterApplication rate barley Active compound (+safener) (g of a.i./ha) (in %)I-13 125  80 60 70 30 50 I-13 + mefenpyr-diethyl 125 + 50  60 60 + 50 5030 + 50 30

Example A-5 Post-Emergence Test

Mefenpyr-diethyl was used as 100 EC and the compound of Ex. No. I-2 wasused as 10 WP.

TABLE A-5 Post-emergence test/greenhouse Damage winter Application ratewheat Active compound (+safener) (g of a.i./ha) (in %) I-2 30 60mefenpyr-diethyl 50 0 I-2 + mefenpyr-diethyl 30 + 50 5 Damage winterApplication rate wheat Active compound (+safener) (g of a.i./ha) (in %)I-13 125 50 mefenpyr-diethyl 50 0 I-13 + mefenpyr-diethyl 125 + 50  10Damage winter Application rate wheat Active compound (+safener) (g ofa.i./ha) (in %) I-15 60 80 mefenpyr-diethyl 50 0 I-15 + mefenpyr-diethyl60 + 50 40 Damage winter Application rate wheat Active compound(+safener) (g of a.i./ha) (in %) I-16 60 25 mefenpyr-diethyl 50 0 I-60 +mefenpyr-diethyl 60 + 50 15 Damage winter Application rate wheat Safener(g of a.i./ha) (in %) mefenpyr-diethyl 50 0 Damage winter Applicationrate wheat Active compound (+safener) (g of a.i./ha) (in %) I-2 30 40 1530 8 20 I-2 + mefenpyr-diethyl 30 + 50 20 15 + 50 10  8 + 50 10 Damagewinter Application rate wheat Active compound (+safener) (g of a.i./ha)(in %) I-17 30 70 15 50 8 40 I-17 + mefenpyr-diethyl 30 + 50 40 15 + 5030  8 + 50 20 Damage winter Application rate wheat Active compound(+safener) (g of a.i./ha) (in %) I-14 1 40 0.5 20 I-14 +mefenpyr-diethyl  1 + 50 30 0.5 + 50  10 Damage winter Application ratewheat Active compound (+safener) (g of a.i./ha) (in %) I-18 2 50 1 30I-18 + mefenpyr-diethyl  2 + 50 20  1 + 50 10 Damage winter Applicationrate wheat Active compound (+safener) (g of a.i./ha) (in %) I-15 30 7015 40 8 30 I-15 + mefenpyr-diethyl 30 + 50 10 15 + 50 0  8 + 50 0 Damagewinter Application rate barley Safener (g of a.i./ha) (in %)mefenpyr-diethyl 50 0 Damage winter Application rate barley Activecompound (+safener) (g of a.i./ha) (in %) I-2 30 80 15 70 8 60 I-2 +mefenpyr-diethyl 30 + 50 50 15 + 50 20  8 + 50 10 Damage winterApplication rate barley Active compound (+safener) (g of a.i./ha) (in %)I-17 30 80 15 70 8 70 I-17 + mefenpyr-diethyl 30 + 50 70 15 + 50 60  8 +50 20 Damage winter Application rate barley Active compound (+safener)(g of a.i./ha) (in %) I-14 0.5 30 0.25 10 I-14 + mefenpyr-diethyl 0.5 +50  20 0.25 + 50   0 Damage winter Application rate barley Activecompound (+safener) (g of a.i./ha) (in %) I-18 2 60 1 20 0.5 10 I-18 +mefenpyr-diethyl  2 + 50 20  1 + 50 10 0.5 + 50  0 Damage winterApplication rate barley Active compound (+safener) (g of a.i./ha) (in %)I-15 30 80 15 70 8 60 I-15 + mefenpyr-diethyl 30 + 50 30 15 + 50 20  8 +50 10

1. A composition comprising an active compound combination comprising(a) a compound of formula (I)

or salts thereof, in which Q¹, Q², R¹, R², R³, R⁴ are defined as followsEx. No. Q¹ Q² R¹ R² R³ R⁴ I-2 O O CH₃ CH₃ OCH₃ CH₃

and (b) a crop-plant-compatibility-improving compound of formula (IIe)

wherein R¹³ and R¹⁶ each represent hydrogen, R¹⁷ represents cyclopropyl,(X⁴)_(n) represents 2-methoxy, and (X⁵)_(n) represents hydrogen.
 2. Amethod for controlling undesirable plants comprising allowing aneffective amount of a composition according to claim 1, to act onundesirable plants and/or their habitat.
 3. A process for preparing aherbicidal composition comprising mixing a composition according toclaim 1, with one or more surfactants and/or extenders.
 4. A compositionof claim 1, wherein the ratio of said at least one compound thatimproves crop plant compatibility per part by weight of said compound offormula I or a salt thereof is from 0.1 to 50.